diff --git a/ghost/core/core/frontend/web/middleware/handle-image-sizes.js b/ghost/core/core/frontend/web/middleware/handle-image-sizes.js
index a887cc4342..f565b87e80 100644
--- a/ghost/core/core/frontend/web/middleware/handle-image-sizes.js
+++ b/ghost/core/core/frontend/web/middleware/handle-image-sizes.js
@@ -139,6 +139,11 @@ module.exports = function handleImageSizes(req, res, next) {
         if (err.code === 'SHARP_INSTALLATION' || err.code === 'IMAGE_PROCESSING' || err.errorType === 'NoContentError') {
             return redirectToOriginal();
         }
+
+        if (err.errorType === 'NotFoundError') {
+            return next();
+        }
+
         next(err);
     });
 };
diff --git a/ghost/core/test/e2e-frontend/static-files.test.js b/ghost/core/test/e2e-frontend/static-files.test.js
new file mode 100644
index 0000000000..1072806b9c
--- /dev/null
+++ b/ghost/core/test/e2e-frontend/static-files.test.js
@@ -0,0 +1,25 @@
+const assert = require('assert/strict');
+const {agentProvider} = require('../utils/e2e-framework');
+
+describe('Static files', function () {
+    let frontendAgent;
+    let ghostServer;
+
+    before(async function () {
+        const agents = await agentProvider.getAgentsWithFrontend();
+        frontendAgent = agents.frontendAgent;
+        ghostServer = agents.ghostServer;
+    });
+
+    after(async function () {
+        await ghostServer.stop();
+    });
+
+    it('serves unstyled 404 for non-existing resized + original files', async function () {
+        const response = await frontendAgent
+            .get('/content/images/size/w2000/1995/12/daniel.jpg')
+            .expect(404);
+
+        assert.ok(response.text.includes('NotFoundError: Image not found'));
+    });
+});
diff --git a/ghost/core/test/unit/frontend/web/middleware/handle-image-sizes.test.js b/ghost/core/test/unit/frontend/web/middleware/handle-image-sizes.test.js
index 80777ddd20..348a105af0 100644
--- a/ghost/core/test/unit/frontend/web/middleware/handle-image-sizes.test.js
+++ b/ghost/core/test/unit/frontend/web/middleware/handle-image-sizes.test.js
@@ -3,6 +3,7 @@ const sinon = require('sinon');
 const storage = require('../../../../../core/server/adapters/storage');
 const activeTheme = require('../../../../../core/frontend/services/theme-engine/active');
 const handleImageSizes = require('../../../../../core/frontend/web/middleware/handle-image-sizes.js');
+const errors = require('@tryghost/errors');
 const imageTransform = require('@tryghost/image-transform');
 
 const fakeResBase = {
@@ -673,5 +674,36 @@ describe('handleImageSizes middleware', function () {
                 done();
             });
         });
+
+        it('goes to next middleware with no error if source and resized image 404', function (done) {
+            dummyStorage.exists = async function () {
+                return false;
+            };
+            dummyStorage.read = async function () {
+                throw new errors.NotFoundError({
+                    message: 'File not found'
+                });
+            };
+
+            const fakeReq = {
+                url: '/size/w1000/2020/02/test.png',
+                originalUrl: '/2020/02/test.png'
+            };
+
+            const fakeRes = {
+                redirect() {
+                    done(new Error('Should not have called redirect'));
+                },
+                setHeader() {},
+                type: function () {}
+            };
+
+            handleImageSizes(fakeReq, fakeRes, function next(err) {
+                if (err) {
+                    return done(err);
+                }
+                done();
+            });
+        });
     });
 });